2011 iMac, weird network problem.

Hi all, has anyone run into this before?

Here is the setup:
iMac is connected wirelessly to my network and connected via wired ethernet to my NAS. My NAS is connected to my network wirelessly. The wireless and wired (iMac directly to NAS) connections are on different networks. On my iMac my wireless is setup as primary and wired ethernet as secondary in the "service order".

Problem:
If I boot this way neither work. If I boot with the ethernet cable detached wireless works. If I reconnect the cable without rebooting then wired works although in my network properties it says that my ethernet cable is unplugged. I know it works because I connect to the NAS on a separate network and the lights are all lit.

So basically if I want to keep this config I have to disconnect the ethernet cable when shutting down and plug it in after booting up. Anyone know why??

 

I use dhcp for my wireless network. Since my wired network is a direct connection between both hosts (iMac and NAS) I statically enter the IP information. When I say they are on different networks, I mean they are on separate IP networks.

I had this setup this way with my Windows based laptop before getting the iMac. It allows me to have a fast connection directly to the NAS while still being able to access it on my home network for my other systems.